US2601520A - Dialkenyl alkanephosphonates and polymers thereof - Google Patents
Dialkenyl alkanephosphonates and polymers thereof Download PDFInfo
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- US2601520A US2601520A US101254A US10125449A US2601520A US 2601520 A US2601520 A US 2601520A US 101254 A US101254 A US 101254A US 10125449 A US10125449 A US 10125449A US 2601520 A US2601520 A US 2601520A
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- diallyl
- dialkenyl
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- 229920000642 polymer Polymers 0.000 title description 14
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- -1 hydrocarbon halide Chemical class 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 2
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OMEGHMBBBTYRFT-UHFFFAOYSA-N chloromethylcyclohexane Chemical compound ClCC1CCCCC1 OMEGHMBBBTYRFT-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- OMPAFJMOQBLWGG-UHFFFAOYSA-N tris(ethenyl) phosphite Chemical compound C=COP(OC=C)OC=C OMPAFJMOQBLWGG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
Definitions
- This invention relates to a new class of unsaturated phosphonates. .Moreparticularly. the invention provides unsaturated di'esters of alkan'ephosphonic acids and cyclic hydrocarbonsubstituted alkanephosphonic acids :and the polymers 'ofgsuch diesters.
- the new esters are prepared byreacting unsaturated triesters of phosphorus. acid with the corresponding hydrocarbon halide.
- the reac tion can be expressed byithe equation,
- the new esters have been found "to exhibit properties which are predominantlylthose of unsaturated diesters of saturated aliphatic dibasic acids. They have been found to exhibit a pronounced resistance to burning and to impart a resistance to burning to compositions containingthem asa component of a mixture, in solution, or in the form of achemicallybound component.
- the monomeric compounds of the invention which are colorless, oily liquids have proven to .be unique and particularly valuable plasticizers and modifying agents for many types of polymers.
- the new esters polymerize to form particularly valuable polymers and copolymers having unique characteristics of color, clarity, hardness and resistnce to deterioration.
- the newiesters are compounds o'f'the formula whereeach R representsan unsaturated'hydrocarbon radical and R represents an alkane radical which may be substituted by one or more cycloalkan'e' or aryl radicals.
- Esters in which the radicals represented by R. are the allyl radicals or its terminally unsaturated homologs (radicals of the formula C(R)2C(R):CH2 where each R represents a hydrogen atom or an alkyl radical) are especially suitable.
- dialkenyl alkanephosphonates and dialkenyl aralkanephosphonates in which each alkenyl radical contains the group -C--C:CH2 attached to the oxygen atom constitute particularly valuable subclasses of the new esters.
- Illustrative examples of the compounds provided by the present invention include diallyl butanephosphonate, diallyl phenylmethanephosphonate, dicinriar'nyl methanephosphonate, dimethallyl eicosanephosphonate, divinyl para tolyl-methanephesphonate, divinyl 2-cyclohex ylethaneph'osphonate, po'ly(dia1ly'l *butanephosphonatei, -D0ly(diallyl phenylmethanephospho nate), dimethallyl propanephosphonate-dially1 phthalate copdlymer, diallyl 2 phenylpropanephosphonate diallyl mal'eate copolymer and divinyl pentanephosphonate -vinyl chloride co polymer.
- the reaction is preferably conducted at about the reflux temperature of the reaction mixture under atmospheric pressure.
- Illustrative examples of unsaturated triesters of phosphorus from which thecompounds ofthe presentv invention canbe prepared include triallyl .phosphite, trimethallyl phosphite, trivinyl phosphite, tri-Z-butenyl phosphite, -tri-isopropenylphosphite, tricinn-amyl phosphite and tri- 2-rcyclohex'ylallyl phosphite.
- Illustrative examples .of hydrocarbon halides from which .the compounds of the present .inventioncan be prepared include .butyl chloride, benzyl chloride, .propyl .bromide, para-methylb nzyl iodide, cyclohexylmethyl chloride and tertiary-butyl chloride.
- the polymeric compounds of the present invention are prepared by polymerizing or copolymerizing the monomeric compounds of the invention.
- the polymerization is preferably conducted by heating the compounds in the presence'of; free radicals.
- a wide varietyof procedures for polymerizing "organic compounds in the presence-30f 'free; radicals are known andcan suitably'be'employed to form the" polymericcompounds of the present-invention.
- a particularly suitable procedure "consists of heating the monomers to "bepolymerized in the presenceof a peroxidic compound which 'decomposes to form free radicalsat a temperature at which the monomersand polymers are stable. The mixture is heated at about" the decomposition temperature of the peroxidic compound.
- Illustrative examples of compounds which when heated with the monomeric compounds of the invention or mixtures of polymerizable compounds containing them initiate the formation of the polymers and copolymers provided by the present invention include (ii-tertiarybutyl peroxide, dibenzoyl peroxide, tertiarybutyl hydroperoxide, 2,2-bis(tertiary-butylperoxy) butane, tertiary-butyl perbenzoate and ditertiary-butyl diperoxalate.
- Example I Diallyl phenylmethanephosphonate is produced by refluxing for hours at 130 C. a solution consisting of 126 grams of benzyl chloride and 100 grams of triallyl phosphite. The ester is isolated by a fractional distillation of the reaction mixture.
- the diallyl phenylmethanephosphonate is a colorless, oily liquid having a boiling point of 144-145 C. under 0.5 mm. Hg pressure and a refractive index (n 20/D) of 1.5132.
- the structure of the diallyl phenylmethanephosphonate is verified by the fact that the ester is found to contain 12.3% phosphorus and to have a molecular weight of 264.
- Diallyl butanephosphonate is produced by refluxing for 20 hours at 70 C. a solution consisting of 500 grams of butyl chloride and 100 grams of triallyl phosphite.
- the ester a colorless, oily liquid having a boiling point of 97-99 C. under 2 mm. Hg pressure and a refractive index (nZO/D) of 1.4553, is isolated by a fractional distillation of the reaction products.
- diallyl butanephosphonate is found to contain 15.0% of phosphorus and to have a molecular weight of 212,- in good agreement with the value of 14.2% phosphorus and the molecular weight of 218 calculated from the formula for the product, namely I I Example III
- Poly(dially1 phenylmethanephosphonate) is prepared by heating a solution consisting of 50 grams of diallyl phenylmethanephosphonatev and 0.5 gram of di-tertiary-butyl peroxide at a tem-- perature of 115 C. for 20 hours.
- the colorless, water clear polymer is isolated by extracting or fractionally distilling off the unreacted monomers.
- Example IV Poly(diallyl 'butanephosphonate) is prepared by heating .a solution consisting of 50 grams of diallyl butanephosphonate and 0.5 gram of ditertiary-butyl peroxide at a temperature of 115 C. for 20 hours. The colorless polymer is isolated by extracting or fractionally distilling off the unreacted monomers.
- Example V A solid copolymer of diallyl butanephosphonate and diallyl phthalate is prepared by heating a solution consisting of grams of dially phthalate, 10 grams of diallyl butanephosphonate and 2 grams of benzoyl peroxide for 24 hours at 450 C., 6 hours at 90 C. and 18 hours at C. The polymer is isolated by extracting or fractionally distilling off the unreacted monomers and catalyst.
- a polymer of a dialkenyl alkanephosphonate A dialkenyl carbocyclic-substituted alkanephosphonate.
- a poly of a dialkenyl carbocyclic-substituted alkanephosphonate 8.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Description
Patented June 24, 1952 DIALKENYL ALKANEPHOSPHONATES (AND POLYMERS THEREOF "Denham Harman and Alan R. Stiles,
Berkeley,
Calif., ass'ignors to Shell Development Com,- ;pany, San Francisco, Calif., a corporation of Delaware N Drawing. Application .J une 24,1949,
'Serial No. 101,254
12 Claims. 1
This invention relates to a new class of unsaturated phosphonates. .Moreparticularly. the invention provides unsaturated di'esters of alkan'ephosphonic acids and cyclic hydrocarbonsubstituted alkanephosphonic acids :and the polymers 'ofgsuch diesters.
The new esters are prepared byreacting unsaturated triesters of phosphorus. acid with the corresponding hydrocarbon halide. The reac tion can be expressed byithe equation,
The new esters have been found "to exhibit properties which are predominantlylthose of unsaturated diesters of saturated aliphatic dibasic acids. They have been found to exhibit a pronounced resistance to burning and to impart a resistance to burning to compositions containingthem asa component of a mixture, in solution, or in the form of achemicallybound component. By virtue of the predominantly saturated aliphatic characteristics of their acyl radicals, the monomeric compounds of the invention, which are colorless, oily liquids have proven to .be unique and particularly valuable plasticizers and modifying agents for many types of polymers. The new esters polymerize to form particularly valuable polymers and copolymers having unique characteristics of color, clarity, hardness and resistnce to deterioration.
The newiesters are compounds o'f'the formula whereeach R representsan unsaturated'hydrocarbon radical and R represents an alkane radical which may be substituted by one or more cycloalkan'e' or aryl radicals. 'Such esters .in which the radicals represented by R/are alkenyl havebeen found to provide monomers for .the formation of a preferred class of. polymers, partlcularly when the olefinic group is in a terminal position. Esters in which the radicals represented by R. are the allyl radicals or its terminally unsaturated homologs (radicals of the formula C(R)2C(R):CH2 where each R represents a hydrogen atom or an alkyl radical) are especially suitable. Thus, dialkenyl alkanephosphonates and dialkenyl aralkanephosphonates in which each alkenyl radical contains the group -C--C:CH2 attached to the oxygen atom constitute particularly valuable subclasses of the new esters.
Illustrative examples of the compounds provided by the present invention include diallyl butanephosphonate, diallyl phenylmethanephosphonate, dicinriar'nyl methanephosphonate, dimethallyl eicosanephosphonate, divinyl para tolyl-methanephesphonate, divinyl 2-cyclohex ylethaneph'osphonate, po'ly(dia1ly'l *butanephosphonatei, -D0ly(diallyl phenylmethanephospho nate), dimethallyl propanephosphonate-dially1 phthalate copdlymer, diallyl 2 phenylpropanephosphonate diallyl mal'eate copolymer and divinyl pentanephosphonate -vinyl chloride co polymer.
In preparing the monomeric compounds of the present invention byreacting the corresponding unsaturated triester of phosphorusacid with the corresponding hydrocarbon halide, the reaction is preferably conducted at about the reflux temperature of the reaction mixture under atmospheric pressure.
Illustrative examples of unsaturated triesters of phosphorus from which thecompounds ofthe presentv invention canbe prepared include triallyl .phosphite, trimethallyl phosphite, trivinyl phosphite, tri-Z-butenyl phosphite, -tri-isopropenylphosphite, tricinn-amyl phosphite and tri- 2-rcyclohex'ylallyl phosphite. V
Illustrative examples .of hydrocarbon halides from which .the compounds of the present .inventioncan be prepared include .butyl chloride, benzyl chloride, .propyl .bromide, para-methylb nzyl iodide, cyclohexylmethyl chloride and tertiary-butyl chloride.
The polymeric compounds of the present invention are prepared by polymerizing or copolymerizing the monomeric compounds of the invention. The polymerization is preferably conducted by heating the compounds in the presence'of; free radicals. A wide varietyof procedures for polymerizing "organic compounds in the presence-30f 'free; radicals are known andcan suitably'be'employed to form the" polymericcompounds of the present-invention. A particularly suitable procedure "consists of heating the monomers to "bepolymerized in the presenceof a peroxidic compound which 'decomposes to form free radicalsat a temperature at which the monomersand polymers are stable. The mixture is heated at about" the decomposition temperature of the peroxidic compound.
Illustrative examples of compounds which when heated with the monomeric compounds of the invention or mixtures of polymerizable compounds containing them initiate the formation of the polymers and copolymers provided by the present invention include (ii-tertiarybutyl peroxide, dibenzoyl peroxide, tertiarybutyl hydroperoxide, 2,2-bis(tertiary-butylperoxy) butane, tertiary-butyl perbenzoate and ditertiary-butyl diperoxalate.
The following examples are presented to illustrate in detail procedures by which the compounds provided by the present invention can suitably be prepared. As the compounds provided by the invention can have a variety of different structures, and in some cases can be prepared by other procedures, the invention is not to be construed as limited to the particular materials or conditions specified in the examples.
Example I Diallyl phenylmethanephosphonate is produced by refluxing for hours at 130 C. a solution consisting of 126 grams of benzyl chloride and 100 grams of triallyl phosphite. The ester is isolated by a fractional distillation of the reaction mixture. The diallyl phenylmethanephosphonate is a colorless, oily liquid having a boiling point of 144-145 C. under 0.5 mm. Hg pressure and a refractive index (n 20/D) of 1.5132. The structure of the diallyl phenylmethanephosphonate is verified by the fact that the ester is found to contain 12.3% phosphorus and to have a molecular weight of 264. These figures are in good agreement with the value of 12.2% phosphorus and the molecular weight of 253 calculated from the formula for the product, namely Example II Diallyl butanephosphonate is produced by refluxing for 20 hours at 70 C. a solution consisting of 500 grams of butyl chloride and 100 grams of triallyl phosphite. The ester, a colorless, oily liquid having a boiling point of 97-99 C. under 2 mm. Hg pressure and a refractive index (nZO/D) of 1.4553, is isolated by a fractional distillation of the reaction products. The diallyl butanephosphonate is found to contain 15.0% of phosphorus and to have a molecular weight of 212,- in good agreement with the value of 14.2% phosphorus and the molecular weight of 218 calculated from the formula for the product, namely I I Example III Poly(dially1 phenylmethanephosphonate) is prepared by heating a solution consisting of 50 grams of diallyl phenylmethanephosphonatev and 0.5 gram of di-tertiary-butyl peroxide at a tem-- perature of 115 C. for 20 hours. The colorless, water clear polymer is isolated by extracting or fractionally distilling off the unreacted monomers.
Example IV Poly(diallyl 'butanephosphonate) is prepared by heating .a solution consisting of 50 grams of diallyl butanephosphonate and 0.5 gram of ditertiary-butyl peroxide at a temperature of 115 C. for 20 hours. The colorless polymer is isolated by extracting or fractionally distilling off the unreacted monomers.
Example V A solid copolymer of diallyl butanephosphonate and diallyl phthalate is prepared by heating a solution consisting of grams of dially phthalate, 10 grams of diallyl butanephosphonate and 2 grams of benzoyl peroxide for 24 hours at 450 C., 6 hours at 90 C. and 18 hours at C. The polymer is isolated by extracting or fractionally distilling off the unreacted monomers and catalyst.
We claim as our invention:
. Diallyl butanephosphonate.
. Diallyl phenylmethanephosphonate.
. Poly(diallyl butanephosphonate).
A diallyl alkanephosphonate.
A dialkenyl alkanephosphonate.
A polymer of a dialkenyl alkanephosphonate. A dialkenyl carbocyclic-substituted alkanephosphonate.
8. A poly of a dialkenyl carbocyclic-substituted alkanephosphonate.
9. A dialkenyl alkanephosphonate in which both alkenyl radicals contain a lower 2-alkenyl group attached to the oxygen atom.
10. A dialkenyl arylalkanephosphonate in which both alkenyl radicals contain a lower 2-alkenyl group attached to the oxygen atom.
11. A phosphonic acid ester having the structure defined by the formula REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,397,422 Kosolopoff Mar. 26, 1946 2,425,766 Fon Toy Aug. 19, 1947 OTHER REFERENCES Kosolopoff: J. Am. Chem. Soc., 67, 2259-60. (Dec. 1945).
Chem. and Eng. News, 25, page 2030, July 14,
Fon Toy: J. Am. Chem. Soc.,.70, 1948).
186-188, (Jan.
Claims (1)
11. A PHOSPHONIC ACID ESTER HAVING THE STRUCTURE DEFINED BY THE FORMULA R''-P(OR)2 IN WHICH EACH R REPRESENTS A MONO-OLEFINICALLY UNSATURATED HYDROCARBON RADICAL AND R'' REPRESENTS A MEMBER OF THE GROUP CONSISTING OF ALKANE RADICALS AND CARBOCYCLIC-SUBSTITUTED ALKANE RADICALS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US101254A US2601520A (en) | 1949-06-24 | 1949-06-24 | Dialkenyl alkanephosphonates and polymers thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US101254A US2601520A (en) | 1949-06-24 | 1949-06-24 | Dialkenyl alkanephosphonates and polymers thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2601520A true US2601520A (en) | 1952-06-24 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US101254A Expired - Lifetime US2601520A (en) | 1949-06-24 | 1949-06-24 | Dialkenyl alkanephosphonates and polymers thereof |
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| Country | Link |
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| US (1) | US2601520A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714100A (en) * | 1952-08-05 | 1955-07-26 | Victor Chemical Works | Diallyl monochloromethanephosphonate and polymers |
| US2735789A (en) * | 1956-02-21 | Methods of flameproofing therewith | ||
| US2811469A (en) * | 1952-08-05 | 1957-10-29 | Victor Chemical Works | Fabric flameproofing process |
| US2867610A (en) * | 1953-09-22 | 1959-01-06 | Victor Chemical Works | Polymers and copolymers of dialkenyl beta-(carboxyalkyl) alkanephosphonates |
| US5128333A (en) * | 1989-12-19 | 1992-07-07 | Regents Of The University Of California | Alkyl substituted phosphates and phosphonates as disruptants of insect sex pheromone-mediated behavior |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2397422A (en) * | 1945-03-24 | 1946-03-26 | Monsanto Chemicals | Esters of paraffin phosphonic acids |
| US2425766A (en) * | 1945-10-29 | 1947-08-19 | Victor Chemical Works | Unsaturated alkyl esters of alkenyl phosphonic acids |
-
1949
- 1949-06-24 US US101254A patent/US2601520A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2397422A (en) * | 1945-03-24 | 1946-03-26 | Monsanto Chemicals | Esters of paraffin phosphonic acids |
| US2425766A (en) * | 1945-10-29 | 1947-08-19 | Victor Chemical Works | Unsaturated alkyl esters of alkenyl phosphonic acids |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2735789A (en) * | 1956-02-21 | Methods of flameproofing therewith | ||
| US2714100A (en) * | 1952-08-05 | 1955-07-26 | Victor Chemical Works | Diallyl monochloromethanephosphonate and polymers |
| US2811469A (en) * | 1952-08-05 | 1957-10-29 | Victor Chemical Works | Fabric flameproofing process |
| US2867610A (en) * | 1953-09-22 | 1959-01-06 | Victor Chemical Works | Polymers and copolymers of dialkenyl beta-(carboxyalkyl) alkanephosphonates |
| US5128333A (en) * | 1989-12-19 | 1992-07-07 | Regents Of The University Of California | Alkyl substituted phosphates and phosphonates as disruptants of insect sex pheromone-mediated behavior |
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